Name: __________________________________ Date: ___________________

Targets and Goals for Chapter 3:General Outcome: Students will describe the properties of simple hydrocarbons and describe hydrocarbon-based industrial processes that are important in Alberta.

- identify materials used in daily life that are based upon Alberta’s petrochemical industry and that involve changes in energy; e.g., plastics, cosmetics, gasoline

- identify the physical characteristics of hydrocarbons, including trends with respect to melting and boiling points and solubility of alkanes, alkenes and alkynes

- provide International Union of Pure and Applied Chemistry (IUPAC) names and structural formulas for simple and noncyclic hydrocarbons in the homologous series of alkanes, alkenes and alkynes that contain up to eight carbon atoms in the parent chain

- identify hydrocarbons as a source of fossil fuels and explain the processes of fractional distillation to refine petroleum and catalytic cracking to produce ethene (ethylene)

- classify, balance and apply mole ratios to important hydrocarbon reactions:o combustion of hydrocarbons to produce carbon dioxide, water vapour and energyo production of ethene (ethylene) from catalytic crackingo hydrogenation of alkenes (unsaturated) to produce alkanes (saturated)o polymerization of ethene (ethylene) to polyethene (polyethylene).

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Chapter 3: Organic Chemistry

Unit A: Chemic

al Changes

Booklet 3 of 3 in Chemistry

Organic refers to substances created by living things!

Chemistry refers to the study of matter!

SO….. Organic Chemistry must mean the study of matter created by living things!

- Organic Chemistry is the study of compounds composed of ____________________________

o Examples of carbon based substances: Gasoline for cars Plastics used to make sports equipment Medications (Advil and Tylonol) Molecules that make up your body

1. Draw the BOHR diagram for Carbon

2. Draw the Lewis Dot diagram for Carbon

3. What is the maximum number of bonds that carbon can have at any given time?

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Organic Chemist

Hydro-Carbon!

4. Draw the BOHR diagram for Hydrogen

5. Draw the Lewis Dot diagram for Hydrogen

6. What is the maximum number of bonds that hydrogen can have at any given time?

Closely study the molecular model on the right. The black circles represent carbon, and the white circles represent hydrogen.

Draw the Lewis Dot Diagram of this molecule.

How many hydrogen atoms does it take to stabilize all of the carbon atoms in this molecule?

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Models

Write the chemical formula for this compound.

- __________________________ are what we will be dealing with in this chapter. o Hydrocarbons are substances made up of only _________________ and __________________

- We will be looking at a few different types of hydrocarbons

SINGLE BONDS

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Hydroca

(_________________)

DOUBLE BONDS

(_________________)

TRIPLE BONDS

(________________)

-ane, -ene, -yneName FormulaMETH 1 CarbonETH 2 CarbonsPROP 3 CarbonsBUT 4 CarbonsPENT 5 CarbonsHEX 6 CarbonsHEPT 7 CarbonsOCT 8 CarbonsNON 9 Carbons

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Naming…….

DEC 10 Carbons

A. SINGLE BONDS End with _______________________________

__________________________________________________________________________________________________

B. DOUBLE BONDS End with _____________________________________

__________________________________________________________________________________________

C. TRIPLE BONDS End with ________________________________________

__________________________________________________________________________________________

Saturated vs. Unsaturated:- ____________________________________ - only single bonds between carbon atoms

- ________________________________ - one or more double or triple bonds between carbon atoms

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How do we know how to draw them with a single, double or triple bond?CnH(2n+2) All single bonds

CnH(2n) One double bond, all the rest are single

CnH(2n-2) One triple bond, all the rest are single

Examples: Will there be single, double or triple bonds???A. C6H14

B. C6H10

C. C5H10

Practice Drawing:

Chemical Formula Drawing Saturated or Unsaturated

C5H12

C5H10

C5H8

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Alkane

Alkene

Alkyne

C6H14

C6H12

**HOW DO WE KNOW HOW MANY HYDROGENS TO ATTACH TO A CARBON????? IS THERE A MAXIMUM???

Alkanes- saturated hydrocarbons- generic formula is C2Hn+2

- find the longest continuous chain of carbons...this is the parent chain. Name it by the number of carbons (1=meth, 2=eth, 3=prop...). End the name in  'ane'

Examples:

Method 1:

C-C-C-C C-C-C C-C-C-C

C C8

C

Method 2:

Method 3: Line Formula

Name Molecular Formula Expanded Structure Condensed Formula Line Formula

Methane

Ethane

Propane

Butane

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Pentane

Hexane

Heptane

Octane

Nonane

Decane

Branched Alkanes:- alkane with smaller carbon groups attached (___________________________________)- Find the longest continuous chain of carbon atoms -  this  is the _______________________________.- Name the parent chain just like you would for the continuous alkanes- Circle the branches (alkyl groups)- Name each alkyl group using the prefix that corresponds to the number of carbons (1 = meth,

 2 = eth...) and use the suffix 'yl’- Number the carbons on the parent chain to show the location of each alkyl group (number them so

that the alkyl groups occur at the lowest carbon number possible)

To put the name all together:

- start with the alkyl groups. Put them in alphabetical order (order them by the alkyl,   not the carbon number).

- number the alkyl groups, using commas between numbers and hyphens between numbers and letters.

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Examples:

Branched Alkenes and Alkynes- Alkenes - unsaturated hydrocarbon containing one or more carbon-carbon double bond

- Alkyne - unsaturated hydrocarbon containing one or more carbon-carbon triple bond

Naming these branches:- alkenes end in “ene,” alkynes end in “yne”- the double or triple bond must be included in the parent chain (it cannot be in a branch)- number the chain so that the carbons with the double or triple bond receive the lowest number

possible- write the name of the parent chain. Indicate where the double or triple bond is by including the

number in between the prefix and the suffix.o Eg. but-1-ene --the double bond is between carbon 1 and 2

- Find any branches off of the parent chain and name them in the same way as you did for alkanes.

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Some More Examples:

C – C – C

C – C – C

C – C

C

C = C – C – C – C – C

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C

C

C

C – C – C – C – C = C

C

C

C

C – C – C – C – C – C = C

C

C

Working Backwards:

6 – ethyl-4,5-dimethyloct-2-yne

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PRACTICE: Page 119 #15, Page 120 #16, Page 121 #4 & 5, Page 129 #28 & 29

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Write the systematic names for the following hydrocarbon compounds.

H H

H – C – C – H _________________________________________

H H

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Quick Review: Naming Hydroca

rbons

H H H

C = C – C – H __________________________________________

H H

Draw the structural diagram for each compound given.

2,2-dimethylpropane

2-methlyprop-1-ene

You will use molecular models to represent various hydrocarbons and suggest how their structure might influence their properties

PROCEDURE:

Step 1: read through the analysis questions so you know what to look for as you build your models

Step 2: use the molecular kit to construct each of the following molecules.

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**** Remember, the black circles represent carbon and the yellow circles represent hydrogen. The connecters between the circles represent the bonds.

Analysis:

1. Which model is the most rigid?

2. Which model is most flexible?

3. On which model are the bonds under the most stress?

4. One which model are the bonds under the least stress?

5. Which model has the largest mass? Which has the smallest?

6. Choosing between hydrocarbons with single, double, or triple bonds, which group will have bonds that are easiest to break? Support your answer.

7. Choosing between hydrocarbons with single, double, or triple bonds, which group will have bonds that are most difficult to break? Support your answer.

8. Which of the three hydrocarbons will have the greatest reactivity? Explain how you came to your conclusion.

9. Order the molecules from most reactive to least reactive.

Page 131

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Try This Activity!

Fact 1:

- ________________________ and ____________________________ of hydrocarbons increase as the number of carbons increase

o BUT WHY? As there is more carbon and hydrogen atoms, there is a greater attraction between

them so they are harder to break apart More energy (heat!) is required to move something with greater mass

Fact 2:

- __________________________ hydrocarbons (double and triple bonds) are more reactive than _______________________ hydrocarbons (single bonds)

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Hydroca

Practice:

1. For each group, order the compounds from most to least reactivea. Hex-2-ene, hex-2-yne, hexane

b. Propane, ethane, but-2-yne

c. Oct-3-yne, heptane, hex-2-ene

- _______________________ is liquid hydrocarbons formed over millions of year from the remains for ancient microscopic __________________________________.

o Petroleum is kind of like a soup of hydrocarbon molecules.- When petroleum is pumped out of the ground, it is separated into its different hydrocarbon molecules

o Each component is a mixture of smaller molecules called _________________________. The process of separating petroleum into different fractions is called _______________.

Here is a jar of wood chips, sand, salt and iron fillings. Imagine this is our unrefined petroleum. How can we separate each type of substance into its fractions?

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Petroleum

__________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________________

This may have been an easy task to figure out – with petroleum it is not as easy as just using a magnet or a filter. How does it work?

- Using the different ____________________________ of hydrocarbons to separate out into ____________________ in order to ____________________.

How it works!

1. The petroleum is vaporized in a hot furnace2. The petroleum vapour is placed into a tall column3. The hot vapours rise inside the column. As the vapour moves away from the heat source, it cools.4. As the vapour cools, it not only drops in temperature, but the molecules condense to form liquids at

different places in the tower. By condensing at different locations in the tower, the fractions can be collected separately.

5. Fractions with high boiling points – the largest molecules in the mixture – will condense first at the bottom of the column. Fractions with lower boiling points will condense higher in the column.

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Fraction

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The breaking up of larger hydrocarbons to form smaller molecules is called _________________________.

HOW CAN A HYDROCARBON CRACK?

1. _____________________________ a. Using a catalyst and lower pressure and temperature

2. ____________________________ a. Using high pressure and temperature

- Hydrocarbons can be used as fuelso Example: Propane is used in campers and

BBQs all the time!

What do you need for combustion to occur?

1. Fuel (hydrocarbon)2. Oxygen (O2(g))

What does combining a fuel and oxygen create?

1. Carbon Dioxide2. Water Vapour

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Cracking under the pressure!

COMBUSTION!

Balancing Hydrocarbon Combustion Reaction Equations:

Balance each equation for a combustion reaction.(a) C2H6(g) + O2(g) CO2(g) + H2O(g)

(b) C3H8(g) + O2(g) CO2(g) + H2O(g)

(c) C6H14(g) + O2(g) CO2(g) + H2O(g)

(d) C8H18(g) + O2(g) CO2(g) + H2O(g)

(e) C2H2(g) + O2(g) CO2(g) + H2O(g)

(f) C2H4(g) + O2(g) CO2(g) + H2O(g)

Write a balanced chemical equation to represent each reaction described below.(a) Candle wax, C25H52, is burned to produce carbon dioxide and water.

(b) Sucrose, C12H22O11, is burned to produce carbon dioxide and water.

23Chapter Review:

Page 153, #1,3,4,6,7,8

Hydrocarbon Naming Review

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Chapter Review:

1. Name the alkanes represented by the structural formulas below:

a.

b.

c.

2. Write the complete structural formula for the following alkanes: a. 2-methylpentane

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b. 2,2-dimethylpropane

c. 3-ethyl-2,5-dimethylheptane

d. 3-ethylpentane

Name the following alkenes from their condensed structural formulas.

1.

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2.

3.

4.

5.

Practice Problems:

Write the condensed structural formula for the following hydrocarbons:

1. 2, 3-dimethylpentane

2. 2-methylpropene27

3. penta-1,2-diene

4. hept-3-yne

5. buta-1,3-diene

6. 2-methylbut-1-ene

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